Journal of Olly Headey. Co-founder & CTO at FreeAgent.

A Startup Story: The FreeAgent Years, 2007-2021

November 16th, 2021
I recently announced my decision to leave FreeAgent, the company I co-founded in 2007. It's been a difficult decision to make as I love FreeAgent dearly – I’m part of the furniture almost – but it’s the right time for me to hang up my well-worn CTO boots. I wanted to write a few words for posterity, so here are some of my memories from our rollercoaster journey. 

FreeAgent Central home page, March 2007. Balloon!

Balancing The Grind

November 11th, 2021
Self portrait take #1232

I was invited by Hao to do an interview about work/life balance on his popular Balance The Grind website recently. I received lots of nice feedback via my LinkedIn post so I thought I’d post the link up on this blog for any readers who don’t inhabit social networks, ‘professional’ ones or otherwise.

You can read the interview here. I would love to hear your feedback on how you approach work/life balance.

Salary Roulette

September 14th, 2021
Job ads which feature salary bands have been shown to be more inclusive and result in a larger number of applicants. Salary transparency is a staff motivator and increases engagement, so why are most companies still keeping rates secret?

HEY vs Fastmail: One year on

May 22nd, 2021

For all the social media, messaging, and productivity apps I have installed, my digital communication is still dominated by email. Sure I use WhatsApp, iMessage, Slack, Basecamp, Twitter, Instagram… but email is the constant that I can’t do without, at work or at home.

I’ve been using Fastmail for around 7 years, and before that I used Gmail. When HEY launched just over a year ago I signed up as soon as I could. Not because Fastmail had flaws, but because I quite like new shiny things, I love Ruby on Rails, and I’m intrigued by the products that Basecamp create. I don’t think Basecamp have the slickest products on the market by any means (they really don’t), but they create a narrative around their products and I found the promotion around HEY quite compelling.

I’ve used HEY for almost a year now, so it feels like the right time to reflect on the product. I should admit that I haven’t use HEY exclusively over this time. I did try forwarding all my email into it for a few weeks, but I found it something of a trial by fire and I quickly reverted. Instead I started to move different cohorts of email over to it (newsletters, GitHub notifications, receipts), enough to give me a solid experience of it without committing full time.

I wrote a popular post last year that has had thousands of views, and I think all those first impressions still stand today. What follows is a breakdown of what works for me with HEY, what doesn’t, and why I’ve ultimately decided it’s not for me.

Boosting the signal

March 9th, 2021
I had a day "out of the office" yesterday (not to be confused with the previous 360 consecutive days out of the physical office since March 13, 2020). I just had a day off, which shouldn't be a particularly big deal. If anything urgent happened I would have received a phone call, otherwise I should easily be able to catch up with things on my return. I filter my email so it's a pleasant place these days, even after a few days without checking. Slack, on the other hand, is a complete disaster zone.

A reminder that the days are long but the decades are short

February 15th, 2021
I seem to happen upon this blog post from Sam Altman every year or so and it always resonates with me. 36 thoughts on life from a 30-year-old (at the time) who appears wise beyond his years. Reading it is life detox. So go ahead and cleanse.

How I implemented custom domain support with automatic TLS certs for my SaaS app

February 14th, 2021
Managing hosting and TLS certificates for customer-specified domains can be a challenge. In this article I explain how I solved this, with relative ease, for

Update 28 Nov 2021: Add disclaimer regarding the reverse proxy to Heroku example
Update 8 Oct 2021: Include instructions for simpler Caddy install

When I first started working on Blogline (a fast, minimalist blogging platform), I had only planned to use it for my own blogs. Like most app developers (certainly those using Rails), I originally hosted it on Heroku, which has decent support for TLS if you're working with only a handful of known domains. Once I'd finished the early prototype, I decided it might be fun to turn it into a SaaS product that would allow customers to create a blog on their own domain in seconds. This didn't sound complicated technically – the main problem was how to manage TLS certificates.

📪 Free your Gmail Inbox

January 8th, 2021

Your inbox is probably a noisy place that you don't enjoy visiting. Am I right? I recently read the following tweet which motivated me to clear out my work inbox for 2021 (I only use Gmail for work).

You can do the same thing in Fastmail, Yahoo or whatever, but here’s how I did it in Gmail. If you’re using HEY this entire post is probably irrelevant! 

Music in 2020

December 28th, 2020
I thought about writing a “2020 in Review” article that was just a blank page, but rather than being facetious I thought I'd write about some of the music I listened to instead.

The problem with acronyms

December 10th, 2020
Reducing the use of unnecessary acronyms in your business will increase productivity and employee happiness, and reduce cynicism as you grow. Here's how.

Confusing vernacular isn’t a new thing to me, but I’ve noticed that an acronym[1] population steadily increases as projects, or entire companies, expand. I can sort of understand. When a company is bigger, there are more people and more things going on. More projects, more meetings, more presentations. Typing “Engaged User Growth Hack” becomes tedious the 14th time you write it in your proposal, so someone initialises it (EUGH) the first time and uses the acronym there on in. Once the document is circulated, it’s inevitable that at some point – it might take a few meetings, but eventually – it becomes common parlance. "How is the EUGH rate looking this week, Ted?"

One of the many problems you’re going to encounter in a growing business is a lack of clarity among staff. A successful business is one where employees understand things, and when they don’t it's okay because they know where to go to find the information required to understand things. 

Whether you’re a new hire reviewing an onboarding guide on your first day, or a seasoned employee reading the latest project proposal, you’re probably going to be faced with a sea of acronyms. The more there are, the more confused you'll be. This is bad for morale and bad for business, so it's your job as a leader in an organisation to spare everyone from this misery by eliminating acronyms as much as possible in your organisation. Here are my top tips.